Wrong Until It Counted: "Churchill: Walking with Destiny" by Andrew Roberts

From September 1940, Winston Churchill lunched privately with King George VI, with no staff present, most Tuesdays when both men were in London, and afterward the King wrote up what had been said. Andrew Roberts was the first Churchill biographer allowed to read those entries. Among what he found was the Prime Minister's private assessment of how the American fleet had been positioned at Pearl Harbor — a view Churchill could not express publicly in 1941.

Churchill: Walking with Destiny is a single-volume life running to roughly 1,100 pages, published by Allen Lane in Britain and Viking in the United States in 2018. Roberts draws on more than forty sources unavailable to previous biographers, of which the King's wartime diary is the most consequential. It took the silver medal in the Council on Foreign Relations' 2019 Arthur Ross Book Award.

The title is Churchill's own phrase for the night of 10 May 1940, and Roberts builds the book around it. His argument is that the preceding sixty-five years were not a prelude interrupted by failure but an apprenticeship conducted through failure: a man wrong about the Dardanelles, wrong about the gold standard, wrong about India and wrong about the abdication was, in 1940, right about the one question that decided everything — and right partly because of what the earlier errors had cost him.

The argument is serious and largely persuasive. Roberts is also an admirer of his subject, and the contested judgments on India and Gallipoli deserve to be weighed alongside his extensive sourcing. Priced accordingly, this is the best one-volume Churchill available.

What the book actually covers

The structure is a straightforward chronology running from 1874 to 1965. Roberts moves fast through Harrow, Sandhurst, Omdurman and the South African escape that made Churchill famous at twenty-five, then slows for the decisions that matter: the Admiralty from 1911, the Dardanelles, the return to gold at prewar parity in 1925, the campaign against the India Bill, the rearmament warnings, the war and the 1945 defeat.

The new material sits in the war years and earns its place. The King's diary records the Tuesday lunches from the King's side, and was written independently of Churchill’s later war memoirs, which began to appear in 1948. Where the two diverge, the divergence is itself evidence.

The weakest passages are on India. Piers Brendon, a former Keeper of the Churchill Archives Centre at Churchill College, Cambridge, reviewing the book in Literary Review in October 2018, faulted Roberts for reading Churchill's documented contempt for Indians as provocative humor rather than settled prejudice. That criticism holds up on the evidence he presents. On the Bengal famine of 1943, in which an estimated two million or more people died, Roberts's position is that Churchill and his cabinet did what could be done given Japanese control of Burma and submarines in the Bay of Bengal. That is a defensible reading of a constrained record. It is not the only one. A 2019 study in Geophysical Research Letters, led by Vimal Mishra at the Indian Institute of Technology Gandhinagar, found Bengal in 1943 to be the only one of six major Indian famines since 1870 not linked to soil-moisture drought, which shifts the weight of causation toward policy. Roberts does not let the famine disturb the verdict.

Gallipoli gets a version of the same treatment. Roberts lists it among Churchill's mistakes while spreading the blame for how it was carried out. Those two positions cannot both carry equal weight. Churchill lost the Admiralty in May 1915 and left the government entirely that November, and the Dardanelles Commission, set up in 1916, did not issue its final report until 1919. A reader who wants the failure examined rather than contextualized will find the chapter thin.

Why it matters for your risk posture

Read it for the base-rate problem, which is the book's real subject. Anyone scoring Churchill on track record in 1937 would have marked him down and been right on the evidence then available: Gallipoli; the gold standard restored at $4.86 against Keynes's published warning about unemployment and industrial contraction; the India Bill; the abdication, where on 7 December 1936 he was shouted down in the Commons and colleagues assumed he was finished. He was then correct about the only question that mattered. Track record is necessary and not sufficient. The useful question about someone repeatedly wrong is whether the errors are random or systematic, and whether what they were wrong about resembles the question in front of you.

Read it for what a principal's own account leaves out. Churchill wrote six volumes on the war between 1948 and 1953, and was awarded the Nobel Prize in Literature in 1953. Those volumes are a primary source and a defense brief at once, and they set the terms of the historiography for decades. The King's diary matters because it captures the same rooms from outside the subject's control. The habit transfers: when you take a self-account — a management representation, a founder's version of a dispute, a witness statement — the first question is what independent record exists, kept by someone with no interest in how it reads later.

Read it, finally, for the distinction between access and interpretation. Queen Elizabeth II granted Roberts access to her father's wartime diaries, a substantial addition to the sources available to Churchill biographers. Exceptional access gives a biographer new evidence to examine; the reader still has to assess how that evidence supports each judgment.

Roberts’s base-rate problem is familiar from senior appointments, where a strong candidate’s record usually contains a setback that a board must either discount or weigh. In our executive background investigations we establish what happened in each episode from records and from people who were present. The candidate’s own account is one source among several, much as a reader can set Churchill’s volumes against the King’s diary. A board can then judge whether the errors form a pattern, and whether that pattern bears on the role being filled.

Key takeaways

• A long record of error is not disqualifying, but it has to be diagnosed. What changed in 1940 was the question, not the man.
• Strong evidence and a settled verdict are different things. Roberts's sourcing is exceptional; his conclusions resolve contested points in his subject's favor with unusual consistency.
• A leader's own history is a source and an argument at once. An independent contemporaneous record can help test a principal's later account.
• Ask how a source obtained its access. Roberts was granted access to the King's wartime diaries. Read them alongside the other evidence and assess how they support his interpretation.
• Contested causation stays contested. A biography that settles Bengal 1943 cleanly has settled it too cleanly.

About the author

Andrew Roberts was born in 1963 and took a first in modern history at Gonville and Caius College, Cambridge, where he later completed a doctorate. His earlier books include Salisbury: Victorian Titan, winner of the Wolfson History Prize, Masters and Commanders, The Storm of War and Napoleon the Great. He is a visiting professor in the Department of War Studies at King's College London and the Bonnie and Tom McCloskey Distinguished Visiting Fellow at the Hoover Institution at Stanford.

Two facts bear on how the book reads. Roberts was created a life peer in November 2022 as Lord Roberts of Belgravia: a biographer of the British establishment who has become part of it. And in a 2019 interview about the biography he named his subject's most compelling quality as his combined moral and physical courage, adding that Churchill "learned from his mistakes" and that "relatively few politicians are able to do that ... and that was a great strength" — the thesis stated plainly. He is not concealing his position; he is arguing it.